Sodium hydride → HCID 21201876, Verbindung

HRID 1979420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979420
[H-].[Na+].[O:3]=[C:4]1[NH:10][C:9]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=2[N:7]([C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][CH:5]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Br[CH2:31][C:32]([C:34]1[O:35][CH:36]=[CH:37][CH:38]=1)=[O:33]>O1CCCC1>[O:35]1[CH:36]=[CH:37][CH:38]=[C:34]1[C:32]([CH2:31][N:10]1[C:9]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=2[N:7]([C:16](=[O:21])[C:17]([CH3:20])([CH3:18])[CH3:19])[CH2:6][CH:5]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:4]1=[O:3])=[O:33]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27950762-Bromo-1-furan-2-yl-ethanoneHCID 212015442-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 21201876HCID 21201876, VerbindungAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

60% Sodium hydride (320 mg) was suspended in tetrahydrofuran (30 ml), under ice-cooling 2-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.00 g) obtained from Step I of Example 89, and the mixture was stirred for 30 minutes. Bromomethyl(furan-2-yl)ketone (1.89 g) was added dropwise thereto, stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (100 ml) and ethyl acetate (100 ml) were added, and separated into aqueous layer and organic layer. The aqueous layer was acidified with 1N hydrochloric acid, extracted with ethyl acetate. The extract was combined with the former organic layer. The combined extract was washed with saturated brine, dried over anhydrous magnesium sulfate, subsequently, purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 550 mg of the titled compound.

Aufarbeitung

  1. stirringstirred for 2 hours at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water (100 ml) and ethyl acetate (100 ml)
  3. additionwere added
  4. customseparated into aqueous layer and organic layer
  5. extractionextracted with ethyl acetate
  6. extractionThe combined extract
  7. washwas washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customsubsequently, purified by silica gel column chromatography(chloroform:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-3786dea1b97f480cab4ccefcf3afe455
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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